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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 902573Generated: November 2, 2026

Allyl bromide → HCID 13811728, compound

https://huagongshe.com/reaction/902573

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAllyl bromideHCID 7841—
Reactant3-BromoquinolineHCID 21413—
ReactantAmmonium ChlorideHCID 25517—
ReactantButyllithiumHCID 178418339—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
SolventDiethyl EtherHCID 3283—
SolventHexaneHCID 8058—
SolventEthyl AcetateHCID 8857—
ProductHCID 13811728HCID 13811728—

Reaction Conditions

Temperature-78 °C

Reaction Steps

In an amount of 24.8 mg of copper(I) iodide was added with 9 ml of diethyl ether and 343.5 μl of 3-bromoquinoline, then added dropwise with 1.6 ml of a 1.57 M solution of n-butyllithium in hexane at −78° C., and stirred at −78° C. for 30 minutes. This reaction mixture was added with 71.4 μl of allyl bromide, stirred at −78° C. for 30 minutes, then warmed to 0° C., added with 20 ml of saturated aqueous ammonium chloride, diluted with 20 ml of ethyl acetate, and successively washed twice with 20 ml of saturated aqueous ammonium chloride and once with 20 ml of saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane to ethyl acetate/hexane (1:1)) to obtain 130 mg of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07365174B2
Source datasetuspto-grants-2008_04
ORD IDord-9f99360e1e224cbb92f42dd0b7c7544e
Source noteuspto-grants-2008_04